1-(beta-hydroxyethylamino)-5-naphthol and process of preparing same



Patented May 26, 1936 PATENT OFFICE 1 (5 HYDROXYETH THOL AND PROC SAME YLAMINO) 5 NAPH- ESS OF PREPARING Arthur Howard Knight, Ashton-on-the-Mersey,

England, assignor to Imperial Limited, a corporation of Great dustries Britain N Drawing. Original 1933, Serial No. 69 application November 20,

Chemical Inapplication November 15, 8,222.

Divided and this 1934, Serial No.

753,899. In Great Britain November 17, 1932 Claims.

a division of my oopending 698,222, filed November 15,

This application is application Serial No. 1933.

My present invention relates to the manufacture of a. new dyestuif intermediate.

According to this invention I treat 1-amino-5- naphthol with ethylene ohlorohydrin in an aqueous solution containing a mild alkali (such as calcium carbonate, sodium carbonate, potassium carbonate, trisodium phosphate, sodium acetate), and I thus obtain the hitherto unknown l-p-hydroxyethylamino 5 naphthol in good yield. This compound has the formula:

CHr-CHz-OH It is particularly useful for the production of new azo dyestufi by coupling thereto suitable diazo compounds in acid or alkaline medium.

The invention is illustrated but not limited, by the following examples in which the parts are by weight.

Example I 31.8 parts of 1-amino-5-naphthol, 10.5 parts of chalk (calcium carbonate), 51 parts of aqueous ethylene-chloro-hydrin of 33.5% strength, and 50 parts of methylated spirits are mixed and boiled for 5 hours under a reflux condenser. A nearly clear solution is formed but on cooling the desired product crystallizes. It is filtered off, Washed and dried. The new product is a greyish powder.

Example II The product of Example I is obtained in purer form and more expeditiously by operating as follows:

31.8 parts of 1-amino-5-naphthol, 30 parts of chalk, and 240 parts of aqueous ethylene-chlorohydrin of 33.5% strength are boiled together for 2 hours. By so using a considerable excess of ethylene-chlorohydrin and by suitably adjusting the reaction time a product free from unchanged aminonaphthol is obtained. The reaction mixture is filtered while it is still hot, and

deposits an oily layer which crystallizes on cooling. The crystals are removed and are almost pure 1-fi-hydroxyethylamino-5-naphthol of formula The compound is easily crystallized from aqueous alcohol. It then forms almost colorless crystals of m. p. 144 C.

It will be understood that my invention is susceptible of various modifications without departing from the spirit thereof.

I claim:

1. A process for the'manufacture of a new coupling component for azo dyes which comprises reacting 1-amino-5-naphthol and ethylene chlorohydrin in the presence of a mild alkali in an aqueous medium.

2. A process as claimed in claim 1, in which the mild alkali is calcium carbonate.

3. A process for the manufacture of 1-,B-hydroxyethylamino-5-naphthol which comprises heating together under reflux 1-amino-5-naphthol, calcium carbonate, and aqueous ethylene chlorohydrin, thereafter cooling the mixture and separating the crystalline precipitate.

4. 1-B-hydroxyethylamino-5-naphthol of the formula: H 

